Talk about a dreamboat trip: a seven-night cruise from Chicago to Toronto calls at some of the region’s most impressive destinations, including Michigan’s Mackinac Island. The Yorktown exudes class and comfort, and on-board experts lecture about the history and culture of the stops. Fares start at $4,395, but the all-inclusive trip is worth that once-in-a-lifetime splurge. (800) 257-5767; traveldynamicsinternational.com [2]

Last summer, the first 4 paved miles opened, stretching between the cute town of Glen Arbor and the Dune Climb. When it’s done, the 27-mile nonmotorized trail will run from the northern end of Sleeping Bear Dunes National Lakeshore through Empire and give visitors an up-close way to enjoy this pristine sand-dune-spotted landscape. (231) 941-4300; sleepingbeartrail.org[6]

Part of the ambience of the Second City comedy club is its sparse stage and worn-down decor. But now Second City offers the same caliber of comedy in a more spacious and comfortable theater on the building’s third floor. Plus, guests can try some of the city’s famous foods while they’re there for the show, including an Italian beef sandwich and nationally known Eli’s Cheesecake. No joke! (312) 662-4562; upcomedyclub.com[10]

Part science center, part history museum, part art gallery, this beautiful complex along the Illinois River celebrates past, present and future in thoughtful, sophisticated ways that all ages can enjoy. (309) 686-7000; peoriariverfrontmuseum.org[18]

Settle into a race car seat during a 10-minute movie about the Italian company’s role in motorsports, then explore the 20,000-square-foot museum that includes a simulator of a qualifying run at the nearby Indianapolis Motor Speedway. Paninis and gelato at the on-site Lino’s Coffee shop offer even more to love about this Italian racing oasis. (317) 243-7171; indycarfactory.com[22]

A fun mix of hands-on activities entertains and educates the toddler to early-elementary-school set. Kids can zip down a fire pole, douse virtual flames with a fire hose and climb into a Great Lakes lighthouse. (920) 432-4397; gbchildrensmuseum.org[26]

An $18 million project has given these noisy, lively swimmers a see-through underwater-tunnel home, an 811-seat amphitheater for shows and a high-diving platform that just about guarantees oohs and aahs. (800) 966-8877; stlzoo.org[34]

Opening in spring 2013, the $10 million thrill ride in this Ozarks park promises new records for wood coasters, including the steepest drop (at 81 degrees) and a double barrel roll. (800) 831-4386; silverdollarcity.com[38]

Stucco walls, stone fireplaces, flat-screen TVs and large travertine-tiled baths with heated floors deck the 24 suites that opened to complement the on-site restaurant. In the morning, guests brew Italian java and then enjoy fresh-baked breakfast treats (delivered in a charming wooden box) at the communal table in the shared living room. gervasivineyard.com[42]

A bubbly staff in 1950s-style rockabilly dress (guys in bow ties, girls in polka dots and nerdy glasses) welcomes guests to this Lincoln Park gem. Playful accents—including a front desk made of dresser drawers—in the 184 rooms help you feel like you’re staying with artsy friends rather than in a big-city hotel. Don’t miss the seasonal dishes at fine-dining standout Perennial Virant on the first floor. From $229. (312) 254-4700; hotellincolnchicago.com[46]

British-lit fans find a luxurious respite near Forest Park. Each of the 108 rooms bears the name of an author, and classy Tudor accents throughout complement modern pillowtop mattresses. From $169. (314) 647-7300; cheshirestl.com[50]

A $50 million project has turned a former gold-ore processing plant into a lovely boutique hotel and casino. The complex acknowledges its past with old photos on its walls but recognizes travelers’ desire for plush appointments and restful colors. From $135. (877) 907-4726; deadwoodmountaingrand.com[54]

When we tried to decide which of Cleveland’s new destinations to include on our list this year, we were a bit overwhelmed. How could we tout the Greater Cleveland Aquarium (pictured)and its cool warehouse-feeling maze of tanks in the historic Powerhouse complex but leave out the Museum of Contemporary Art Cleveland? The museum just moved into a hexagonal building in the Uptown neighborhood to better showcase its changing exhibitions. And we couldn’t possibly forget the nearby Cleveland Museum of Art, a free-admission gem in University Circle that will wrap up its ambitious expansion project in 2013. Then there’s the Cleveland Play House, a regional theater company that performs in the recently renovated 506-seat Allen Theatre, a former 3,000-seat movie palace. A few blocks from the internationally renowned Cleveland Clinic, The Tudor Arms Hotel has turned a 1931 Gothic-style property into a boutique DoubleTree hotel with European accents and plush amenities (from $120). And that just reflects some of the $2 billion the city and its investors have spent on tourism infrastructure during the past few years. Ready to go? Contact Positively Cleveland. (800) 719-1311; positivelycleveland.com[62]

With an Out of Africa mystique at the semiprivate Passport Club and northern plains cuisine at the Blue Mountain Smokehouse Grille, an evening here promises great cocktails and smoked meats in a restored barn. (712) 737-3153; bluemt.co[83]

Seasonal ingredients meet unexpected twists, like in the Brandade, a scrumptious dip made from pureed cod; the LHK Salad, enhanced by shavings of licorice-flavor fennel; and noodles topped with fresh asparagus and foraged morels. (317) 663-8063; lateharvestkitchen.com[91]

The next time you’re on the Magnificent Mile, go here for a mind-blowing dry-aged steak dinner. Sides served in hot cast-iron dishes complement outstanding cocktails and memorable sauces. (312) 321-8823; mjshchicago.com[103]

A renovation at the Hyatt Regency produced this new restaurant. Its locally inspired menu ranges from a martini called Purple Rain to a local goat cheese ice cream parfait served in Red Wing Pottery. Try the griddled PB&J made with creamy chestnut butter and Scandinavian-inspired lingonberry jam. (612) 596-4640; prairiekitchenandbar.com[111]

The name? From the grape. The menu of daily features suggests wine pairings for each meat and fish offering, whether it’s seasonal dishes or lamb osso buco and applewood bacon-seared scallops. (920) 406-9463; syrahgb.com[115]

The name is a tongue-in-cheek nod to the owner’s Czechoslovakian heritage and Gordon Ramsay style in the kitchen, but we found nothing evil in the beer, locally sourced food and service. Choose from up to eight microbrews on draft, including the flagship Lucky Dog and the 7 AM (with hints of oatmeal and cream). (574) 842-2663; evilczechbrewery.com [119]

Oh, the irony. An 1880s corset factory once owned by a staunch Prohibitionist has become a place where carefully crafted whiskey, gin, vodka and rum flow freely. (269) 820-2050; journeymandistillery.com[123]

It’s impossible to have a bad night when you can choose from 48 on-tap beers, read The Sunday Times of London, linger over Scotch eggs and toast the wobbly bobby—British slang for a drunken police officer. (605) 721-7468; wobblybobby.com[127]